EP1196137A1 - Systems comprising organosiloxane resins for delivering oral care substances and for prolonging such delivery - Google Patents
Systems comprising organosiloxane resins for delivering oral care substances and for prolonging such deliveryInfo
- Publication number
- EP1196137A1 EP1196137A1 EP00945085A EP00945085A EP1196137A1 EP 1196137 A1 EP1196137 A1 EP 1196137A1 EP 00945085 A EP00945085 A EP 00945085A EP 00945085 A EP00945085 A EP 00945085A EP 1196137 A1 EP1196137 A1 EP 1196137A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- oral care
- delivery
- mixtures
- organosiloxane resin
- group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 229920005989 resin Polymers 0.000 title claims abstract description 73
- 239000011347 resin Substances 0.000 title claims abstract description 73
- 239000000126 substance Substances 0.000 title claims abstract description 68
- 125000005375 organosiloxane group Chemical group 0.000 title claims abstract description 51
- 239000000203 mixture Substances 0.000 claims abstract description 174
- 239000012530 fluid Substances 0.000 claims abstract description 43
- 230000001681 protective effect Effects 0.000 claims abstract description 41
- 210000000214 mouth Anatomy 0.000 claims abstract description 38
- 229920000642 polymer Polymers 0.000 claims abstract description 37
- 229920005645 diorganopolysiloxane polymer Polymers 0.000 claims abstract description 34
- 239000006254 rheological additive Substances 0.000 claims abstract description 26
- 230000003381 solubilizing effect Effects 0.000 claims abstract description 17
- 238000000034 method Methods 0.000 claims abstract description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 39
- 229920001296 polysiloxane Polymers 0.000 claims description 29
- -1 chelants Substances 0.000 claims description 21
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 19
- 229940122957 Histamine H2 receptor antagonist Drugs 0.000 claims description 17
- 239000004215 Carbon black (E152) Substances 0.000 claims description 16
- 229930195733 hydrocarbon Natural products 0.000 claims description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 239000003795 chemical substances by application Substances 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 12
- 230000002087 whitening effect Effects 0.000 claims description 12
- 150000002430 hydrocarbons Chemical class 0.000 claims description 11
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 10
- VKPSKYDESGTTFR-UHFFFAOYSA-N isododecane Natural products CC(C)(C)CC(C)CC(C)(C)C VKPSKYDESGTTFR-UHFFFAOYSA-N 0.000 claims description 9
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 claims description 9
- GTJOHISYCKPIMT-UHFFFAOYSA-N 2-methylundecane Chemical compound CCCCCCCCCC(C)C GTJOHISYCKPIMT-UHFFFAOYSA-N 0.000 claims description 8
- SGVYKUFIHHTIFL-UHFFFAOYSA-N Isobutylhexyl Natural products CCCCCCCC(C)C SGVYKUFIHHTIFL-UHFFFAOYSA-N 0.000 claims description 8
- 239000003963 antioxidant agent Substances 0.000 claims description 8
- 239000003921 oil Substances 0.000 claims description 8
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 claims description 7
- 229940090181 propyl acetate Drugs 0.000 claims description 7
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 7
- 208000006558 Dental Calculus Diseases 0.000 claims description 6
- QBWCMBCROVPCKQ-UHFFFAOYSA-N chlorous acid Chemical class OCl=O QBWCMBCROVPCKQ-UHFFFAOYSA-N 0.000 claims description 6
- 210000003298 dental enamel Anatomy 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- DJXNLVJQMJNEMN-UHFFFAOYSA-N 2-[difluoro(methoxy)methyl]-1,1,1,2,3,3,3-heptafluoropropane Chemical compound COC(F)(F)C(F)(C(F)(F)F)C(F)(F)F DJXNLVJQMJNEMN-UHFFFAOYSA-N 0.000 claims description 5
- FNUBKINEQIEODM-UHFFFAOYSA-N 3,3,4,4,5,5,5-heptafluoropentanal Chemical compound FC(F)(F)C(F)(F)C(F)(F)CC=O FNUBKINEQIEODM-UHFFFAOYSA-N 0.000 claims description 5
- 239000000796 flavoring agent Substances 0.000 claims description 5
- 239000003485 histamine H2 receptor antagonist Substances 0.000 claims description 5
- 235000015097 nutrients Nutrition 0.000 claims description 5
- 229940121363 anti-inflammatory agent Drugs 0.000 claims description 4
- 239000002260 anti-inflammatory agent Substances 0.000 claims description 4
- 239000004599 antimicrobial Substances 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 235000013355 food flavoring agent Nutrition 0.000 claims description 4
- 235000003599 food sweetener Nutrition 0.000 claims description 4
- 239000003605 opacifier Substances 0.000 claims description 4
- 150000002978 peroxides Chemical class 0.000 claims description 4
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 claims description 4
- 239000000049 pigment Substances 0.000 claims description 4
- 239000003765 sweetening agent Substances 0.000 claims description 4
- 229920002554 vinyl polymer Polymers 0.000 claims description 4
- 239000004698 Polyethylene Substances 0.000 claims description 3
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 230000000202 analgesic effect Effects 0.000 claims description 3
- 239000003086 colorant Substances 0.000 claims description 3
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 claims description 3
- 125000000962 organic group Chemical group 0.000 claims description 3
- 150000004965 peroxy acids Chemical class 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 229920000573 polyethylene Polymers 0.000 claims description 3
- 239000004094 surface-active agent Substances 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- 239000000811 xylitol Substances 0.000 claims description 3
- 235000010447 xylitol Nutrition 0.000 claims description 3
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 claims description 3
- 229960002675 xylitol Drugs 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 230000003078 antioxidant effect Effects 0.000 claims 2
- 239000003443 antiviral agent Substances 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 239000000047 product Substances 0.000 description 17
- 239000000463 material Substances 0.000 description 15
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 14
- 239000003814 drug Substances 0.000 description 14
- 229940079593 drug Drugs 0.000 description 13
- 230000008901 benefit Effects 0.000 description 12
- 229920002050 silicone resin Polymers 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 102000005962 receptors Human genes 0.000 description 8
- 108020003175 receptors Proteins 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- 239000004205 dimethyl polysiloxane Substances 0.000 description 7
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 7
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 7
- 229960001340 histamine Drugs 0.000 description 7
- 239000004615 ingredient Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 229920000388 Polyphosphate Polymers 0.000 description 6
- 235000006708 antioxidants Nutrition 0.000 description 6
- 238000004132 cross linking Methods 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- 239000001205 polyphosphate Substances 0.000 description 6
- 235000011176 polyphosphates Nutrition 0.000 description 6
- 230000000840 anti-viral effect Effects 0.000 description 5
- 229940008099 dimethicone Drugs 0.000 description 5
- 235000011180 diphosphates Nutrition 0.000 description 5
- VTIIJXUACCWYHX-UHFFFAOYSA-L disodium;carboxylatooxy carbonate Chemical compound [Na+].[Na+].[O-]C(=O)OOC([O-])=O VTIIJXUACCWYHX-UHFFFAOYSA-L 0.000 description 5
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical class COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 229940045872 sodium percarbonate Drugs 0.000 description 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 229920004482 WACKER® Polymers 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- AQIXAKUUQRKLND-UHFFFAOYSA-N cimetidine Chemical compound N#C/N=C(/NC)NCCSCC=1N=CNC=1C AQIXAKUUQRKLND-UHFFFAOYSA-N 0.000 description 4
- 239000002537 cosmetic Substances 0.000 description 4
- 235000015872 dietary supplement Nutrition 0.000 description 4
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 description 4
- YECBIJXISLIIDS-UHFFFAOYSA-N mepyramine Chemical compound C1=CC(OC)=CC=C1CN(CCN(C)C)C1=CC=CC=N1 YECBIJXISLIIDS-UHFFFAOYSA-N 0.000 description 4
- 229960000582 mepyramine Drugs 0.000 description 4
- 239000011707 mineral Substances 0.000 description 4
- 235000010755 mineral Nutrition 0.000 description 4
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 4
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 4
- 230000000069 prophylactic effect Effects 0.000 description 4
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
- MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 description 4
- 229940088594 vitamin Drugs 0.000 description 4
- 229930003231 vitamin Natural products 0.000 description 4
- 235000013343 vitamin Nutrition 0.000 description 4
- 239000011782 vitamin Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 3
- 230000001680 brushing effect Effects 0.000 description 3
- 229960001380 cimetidine Drugs 0.000 description 3
- 230000008602 contraction Effects 0.000 description 3
- 230000001419 dependent effect Effects 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 3
- 235000021317 phosphate Nutrition 0.000 description 3
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 230000002035 prolonged effect Effects 0.000 description 3
- 239000011253 protective coating Substances 0.000 description 3
- 230000004044 response Effects 0.000 description 3
- 210000003296 saliva Anatomy 0.000 description 3
- 238000012216 screening Methods 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- FQENQNTWSFEDLI-UHFFFAOYSA-J sodium diphosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O FQENQNTWSFEDLI-UHFFFAOYSA-J 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- AQLJVWUFPCUVLO-UHFFFAOYSA-N urea hydrogen peroxide Chemical compound OO.NC(N)=O AQLJVWUFPCUVLO-UHFFFAOYSA-N 0.000 description 3
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
- WEEGYLXZBRQIMU-UHFFFAOYSA-N 1,8-cineole Natural products C1CC2CCC1(C)OC2(C)C WEEGYLXZBRQIMU-UHFFFAOYSA-N 0.000 description 2
- YFVBASFBIJFBAI-UHFFFAOYSA-M 1-tetradecylpyridin-1-ium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCC[N+]1=CC=CC=C1 YFVBASFBIJFBAI-UHFFFAOYSA-M 0.000 description 2
- BANXPJUEBPWEOT-UHFFFAOYSA-N 2-methyl-Pentadecane Chemical compound CCCCCCCCCCCCCC(C)C BANXPJUEBPWEOT-UHFFFAOYSA-N 0.000 description 2
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 2
- ANAAMBRRWOGKGU-UHFFFAOYSA-M 4-ethyl-1-tetradecylpyridin-1-ium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCC[N+]1=CC=C(CC)C=C1 ANAAMBRRWOGKGU-UHFFFAOYSA-M 0.000 description 2
- FHEHIXJLCWUPCZ-UHFFFAOYSA-N 4-prop-2-enylbenzene-1,2-diol Chemical compound OC1=CC=C(CC=C)C=C1O FHEHIXJLCWUPCZ-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
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- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
- DBVJJBKOTRCVKF-UHFFFAOYSA-N Etidronic acid Chemical compound OP(=O)(O)C(O)(C)P(O)(O)=O DBVJJBKOTRCVKF-UHFFFAOYSA-N 0.000 description 2
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- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 2
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- INVGWHRKADIJHF-UHFFFAOYSA-N Sanguinarin Chemical compound C1=C2OCOC2=CC2=C3[N+](C)=CC4=C(OCO5)C5=CC=C4C3=CC=C21 INVGWHRKADIJHF-UHFFFAOYSA-N 0.000 description 2
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- MBMBGCFOFBJSGT-KUBAVDMBSA-N all-cis-docosa-4,7,10,13,16,19-hexaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O MBMBGCFOFBJSGT-KUBAVDMBSA-N 0.000 description 2
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- FUWUEFKEXZQKKA-UHFFFAOYSA-N beta-thujaplicin Chemical compound CC(C)C=1C=CC=C(O)C(=O)C=1 FUWUEFKEXZQKKA-UHFFFAOYSA-N 0.000 description 2
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- RMRCNWBMXRMIRW-BYFNXCQMSA-M cyanocobalamin Chemical compound N#C[Co+]N([C@]1([H])[C@H](CC(N)=O)[C@]\2(CCC(=O)NC[C@H](C)OP(O)(=O)OC3[C@H]([C@H](O[C@@H]3CO)N3C4=CC(C)=C(C)C=C4N=C3)O)C)C/2=C(C)\C([C@H](C/2(C)C)CCC(N)=O)=N\C\2=C\C([C@H]([C@@]/2(CC(N)=O)C)CCC(N)=O)=N\C\2=C(C)/C2=N[C@]1(C)[C@@](C)(CC(N)=O)[C@@H]2CCC(N)=O RMRCNWBMXRMIRW-BYFNXCQMSA-M 0.000 description 2
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- OVBPIULPVIDEAO-LBPRGKRZSA-N folic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-LBPRGKRZSA-N 0.000 description 2
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- 230000036541 health Effects 0.000 description 2
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- 238000000099 in vitro assay Methods 0.000 description 2
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- 238000010348 incorporation Methods 0.000 description 2
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- 230000005764 inhibitory process Effects 0.000 description 2
- OZWKMVRBQXNZKK-UHFFFAOYSA-N ketorolac Chemical compound OC(=O)C1CCN2C1=CC=C2C(=O)C1=CC=CC=C1 OZWKMVRBQXNZKK-UHFFFAOYSA-N 0.000 description 2
- 229960004752 ketorolac Drugs 0.000 description 2
- 230000003212 lipotrophic effect Effects 0.000 description 2
- 239000003912 lipotropic agent Substances 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229960001047 methyl salicylate Drugs 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 210000004400 mucous membrane Anatomy 0.000 description 2
- 210000003300 oropharynx Anatomy 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 230000035515 penetration Effects 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920000058 polyacrylate Polymers 0.000 description 2
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- WKEDVNSFRWHDNR-UHFFFAOYSA-N salicylanilide Chemical compound OC1=CC=CC=C1C(=O)NC1=CC=CC=C1 WKEDVNSFRWHDNR-UHFFFAOYSA-N 0.000 description 1
- 229950000975 salicylanilide Drugs 0.000 description 1
- 239000001296 salvia officinalis l. Substances 0.000 description 1
- 229940084560 sanguinarine Drugs 0.000 description 1
- YZRQUTZNTDAYPJ-UHFFFAOYSA-N sanguinarine pseudobase Natural products C1=C2OCOC2=CC2=C3N(C)C(O)C4=C(OCO5)C5=CC=C4C3=CC=C21 YZRQUTZNTDAYPJ-UHFFFAOYSA-N 0.000 description 1
- CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical group [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical class O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- IFGCUJZIWBUILZ-UHFFFAOYSA-N sodium 2-[[2-[[hydroxy-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyphosphoryl]amino]-4-methylpentanoyl]amino]-3-(1H-indol-3-yl)propanoic acid Chemical compound [Na+].C=1NC2=CC=CC=C2C=1CC(C(O)=O)NC(=O)C(CC(C)C)NP(O)(=O)OC1OC(C)C(O)C(O)C1O IFGCUJZIWBUILZ-UHFFFAOYSA-N 0.000 description 1
- 235000019830 sodium polyphosphate Nutrition 0.000 description 1
- MWNQXXOSWHCCOZ-UHFFFAOYSA-L sodium;oxido carbonate Chemical compound [Na+].[O-]OC([O-])=O MWNQXXOSWHCCOZ-UHFFFAOYSA-L 0.000 description 1
- YKOLYTVUIVUUDY-UHFFFAOYSA-K sodium;zinc;2-hydroxypropane-1,2,3-tricarboxylate Chemical compound [Na+].[Zn+2].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O YKOLYTVUIVUUDY-UHFFFAOYSA-K 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- ANOBYBYXJXCGBS-UHFFFAOYSA-L stannous fluoride Chemical compound F[Sn]F ANOBYBYXJXCGBS-UHFFFAOYSA-L 0.000 description 1
- 229960002799 stannous fluoride Drugs 0.000 description 1
- 229940102548 stearalkonium hectorite Drugs 0.000 description 1
- 229910001631 strontium chloride Inorganic materials 0.000 description 1
- AHBGXTDRMVNFER-UHFFFAOYSA-L strontium dichloride Chemical compound [Cl-].[Cl-].[Sr+2] AHBGXTDRMVNFER-UHFFFAOYSA-L 0.000 description 1
- WPLOVIFNBMNBPD-ATHMIXSHSA-N subtilin Chemical compound CC1SCC(NC2=O)C(=O)NC(CC(N)=O)C(=O)NC(C(=O)NC(CCCCN)C(=O)NC(C(C)CC)C(=O)NC(=C)C(=O)NC(CCCCN)C(O)=O)CSC(C)C2NC(=O)C(CC(C)C)NC(=O)C1NC(=O)C(CCC(N)=O)NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C1NC(=O)C(=C/C)/NC(=O)C(CCC(N)=O)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)CNC(=O)C(NC(=O)C(NC(=O)C2NC(=O)CNC(=O)C3CCCN3C(=O)C(NC(=O)C3NC(=O)C(CC(C)C)NC(=O)C(=C)NC(=O)C(CCC(O)=O)NC(=O)C(NC(=O)C(CCCCN)NC(=O)C(N)CC=4C5=CC=CC=C5NC=4)CSC3)C(C)SC2)C(C)C)C(C)SC1)CC1=CC=CC=C1 WPLOVIFNBMNBPD-ATHMIXSHSA-N 0.000 description 1
- JEYKZWRXDALMNG-UHFFFAOYSA-N sufotidine Chemical compound CN1N=C(CS(C)(=O)=O)N=C1NCCCOC1=CC=CC(CN2CCCCC2)=C1 JEYKZWRXDALMNG-UHFFFAOYSA-N 0.000 description 1
- 229950002504 sufotidine Drugs 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 229960002180 tetracycline Drugs 0.000 description 1
- 229930101283 tetracycline Natural products 0.000 description 1
- 235000019364 tetracycline Nutrition 0.000 description 1
- 150000003522 tetracyclines Chemical class 0.000 description 1
- RYCLIXPGLDDLTM-UHFFFAOYSA-J tetrapotassium;phosphonato phosphate Chemical compound [K+].[K+].[K+].[K+].[O-]P([O-])(=O)OP([O-])([O-])=O RYCLIXPGLDDLTM-UHFFFAOYSA-J 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 235000019157 thiamine Nutrition 0.000 description 1
- 229960003495 thiamine Drugs 0.000 description 1
- 239000011721 thiamine Substances 0.000 description 1
- KYMBYSLLVAOCFI-UHFFFAOYSA-N thiamine Chemical compound CC1=C(CCO)SCN1CC1=CN=C(C)N=C1N KYMBYSLLVAOCFI-UHFFFAOYSA-N 0.000 description 1
- IUTCEZPPWBHGIX-UHFFFAOYSA-N tin(2+) Chemical compound [Sn+2] IUTCEZPPWBHGIX-UHFFFAOYSA-N 0.000 description 1
- 229950011533 tiotidine Drugs 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 229960003500 triclosan Drugs 0.000 description 1
- UNXRWKVEANCORM-UHFFFAOYSA-I triphosphate(5-) Chemical compound [O-]P([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O UNXRWKVEANCORM-UHFFFAOYSA-I 0.000 description 1
- VSJRDSLPNMGNFG-UHFFFAOYSA-H trizinc;2-hydroxypropane-1,2,3-tricarboxylate;trihydrate Chemical compound O.O.O.[Zn+2].[Zn+2].[Zn+2].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O VSJRDSLPNMGNFG-UHFFFAOYSA-H 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 229940116269 uric acid Drugs 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- 235000019155 vitamin A Nutrition 0.000 description 1
- 239000011719 vitamin A Substances 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 235000019166 vitamin D Nutrition 0.000 description 1
- 239000011710 vitamin D Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 229940045997 vitamin a Drugs 0.000 description 1
- 229940011671 vitamin b6 Drugs 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 239000009637 wintergreen oil Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229950003675 zaltidine Drugs 0.000 description 1
- 229940085658 zinc citrate trihydrate Drugs 0.000 description 1
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Classifications
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Definitions
- the present invention relates to systems for delivering oral care substances to the surfaces of the teeth and for prolonging such delivery. More specifically, the present invention relates to a system comprising a delivery composition comprising organosiloxane resins and at least one oral care substance for delivering the oral care substance, and a protective composition comprised of organosiloxane resins for prolonging the presence of the delivery composition in the oral cavity.
- the delivery composition forms a film on the surface to which it has been applied and provides sustained release of the oral care substance from the film for prolonged therapeutic, prophylactic, and/or cosmetic benefits.
- the systems herein may further provide sustained release benefits to other oral surfaces, such as the gingival and mucosal tissues, as well as to the surfaces of the teeth.
- Oral care products by which various oral care substances or actives can be delivered to the soft and hard tissues of the oral cavity have previously been known.
- oral care products include, for example, brushing aids such as dentifrice products for delivery of anti-caries actives such as fluoride or other actives for the reduction of the bacteria that lead to the formation of plaque, and mouthwashes containing breath freshening actives and/or antibacterial actives.
- bleaching agents such as peroxide that can be applied directly to the surfaces of the teeth, i.e., to the tooth enamel, have been developed.
- the above systems are water-soluble, i.e., they are readily dissolved by saliva, generally within about 1-3 hours after application. Therefore, their degree of durability is low, and they cannot provide long-term delivery of the active ingredient that is present in the composition.
- their water- soluble nature precludes them from being used with oral care actives that would be unstable in water-based films.
- Sodium percarbonate is one example of such an active; it would be unstable in the high pH environment of an aqueous-based film.
- the present invention is directed to systems for delivering an oral care substance to the oral cavity comprising: (a) a delivery composition comprised of: (i) an organosiloxane resin; (ii) a volatile carrier capable of solubilizing the organosiloxane resin; (iii) a rheology modifier; and (iv) at least one oral care substance; and (b) a protective composition comprised of: (i) an organosiloxane resin; and (ii) a volatile carrier capable of solubilizing the organosiloxane resin.
- the protective composition may further comprise a fluid diorganopolysiloxane- based polymer and/or a rheology modifier.
- the present invention is further directed to systems for delivering an oral care substance to the oral cavity comprising: (a) a delivery composition comprised of: (i) an organosiloxane resin; (ii) a fluid diorganopolysiloxane-based polymer; (iii) a volatile carrier capable of solubilizing the organosiloxane resin and the fluid diorganopolysiloxane-based polymer; (iv) a rheology modifier; and (v) at least one oral care substance; and (b) a protective composition comprised of: (i) an organosiloxane resin; and (ii) a volatile carrier capable of solubilizing the organosiloxane resin.
- the protective composition may further comprise a fluid diorganopolysiloxane-based polymer and/or a rheology modifier.
- the present invention further is directed to a method of using these systems.
- the delivery systems herein are comprised of a delivery composition and a protective composition.
- the delivery and protective compositions herein comprise essential components, as well as optional components. The essential and optional components of these compositions of the present invention are described in the following paragraphs.
- the delivery composition herein is a composition for delivering an oral care substance to the oral cavity.
- the delivery composition comprises an oral care substance for providing a therapeutic, prophylactic, and/or cosmetic benefit to the oral cavity.
- One preferred embodiment of the delivery composition is comprised of an organosiloxane resin; a volatile carrier capable of solubilizing the organosiloxane resin; a rheology modifier; and at least one oral care substance.
- Another preferred embodiment of the delivery composition is comprised of an organosiloxane resin; a fluid diorganopolysiloxane-based polymer; a volatile carrier capable of solubilizing the organosiloxane resin and the fluid diorganopolysiloxane-based polymer; a rheology modifier; and at least one oral care substance.
- the protective composition acts as a protective coating to prolong the presence of the oral care substance or substances contained in the delivery composition in the oral cavity.
- the protective composition need not comprise an oral care substance.
- One preferred embodiment of the protective composition is comprised of an organosiloxane resin and a volatile carrier capable of solubilizing the organosiloxane resin.
- a rheology modifier may also be present.
- the protective composition is comprised of an organosiloxane resin, a fluid diorganopolysiloxane-based polymer, a volatile carrier capable of solubilizing the organosiloxane resin and the fluid diorganopolysiloxane-based polymer.
- a rheology modifier may also be present.
- the protective composition need not comprise an oral care substance in order to act as a protective coating for the delivery composition. However, it should be noted that any of the oral care substances described herein could additionally be added to the protective composition. It should also be noted that more than one application of the protective composition, following the application of the delivery composition, can be made.
- Silicone resins are highly crosslinked polymeric siloxane systems.
- the crosslinking is introduced through the incorporation of tri-functional and tetra- functional silanes with mono-functional or di-functional, or both, silanes during manufacture of the silicone resin.
- the degree of crosslinking that is required in order to result in a silicone resin will vary according to the specific silane units incorporated into the silicone resin.
- silicone materials which have a sufficient level of trifunctional and tetrafunctional siloxane monomer units, and hence, a sufficient level of crosslinking, such that they dry down to a rigid, or hard, film are considered to be silicone resins.
- the ratio of oxygen atoms to silicon atoms is indicative of the level of crosslinking in a particular silicone material.
- Silicone materials which have at least about 1.1 oxygen atoms per silicon atom will generally be silicone resins herein.
- the ratio of oxygen:silicon atoms is at least about
- Silicone materials and silicone resins in particular can conveniently be identified according to a shorthand nomenclature system well known to those skilled in the art as the "MDTQ" nomenclature. Under this system, the silicone is described according to the presence of various siloxane monomer units which make up the silicone. Briefly, the symbol M denotes the mono-functional unit (CH3)3SiO)_5; D denotes the difunctional unit (CH3)2SiO; T denotes the trifunctional unit (CH3)SiO-
- Si ⁇ 2- Note that a small amount, up to about 5% of silanol or alkoxy functionality may also be present in the resin structure as a result of processing.
- Primes of the unit symbols denote substituents other than methyl, and must be specifically defined for each occurrence. Typical alternate substituents include groups such as vinyl, phenyl, amino, hydroxyl, etc.
- the molar ratios of the various units either in terms of subscripts to the symbols indicating the total number of each type of unit in the silicone, or an average thereof, or as specifically indicated ratios in combination with molecular weight, complete the description of the silicone material under the MDTQ system. Higher relative molar amounts of T, Q, T' and/or Q' to D, D', M and/or M' in a silicone resin is indicative of higher levels of crosslinking. As discussed before, however, the overall level of crosslinking can also be indicated by the oxygen to silicon ratio.
- the organosiloxane resins are solid at about 25°C and the average molecular weight of the resins is from about 1 ,000 to about 10,000.
- the resins are soluble in organic solvents such as toluene, xylene, isoparaffins, and cyclosiloxanes or the volatile carrier described below, indicating that the resin is not sufficiently crosslinked such that the resin is insoluble in the volatile carrier.
- the silicone resins preferred for use herein are MQ, MT, MTQ, and MDTQ resins; such MQ resins are disclosed in U.S. Patent 5,330,747, Krzysik, issued July 19, 1994.
- the preferred silicone substituent is methyl.
- MQ resins wherein the M:Q ratio is from about 0.5:1.0 to about 1.5:1.0.
- Organosiloxane resins such as these are commercially available, for example, Wacker 803 and 804 available from Wacker Silicones Corporation of Adrian, Michigan, US, and G.E. 1170-002 from the General Electric Company.
- the level of the resin that is used in the compositions is dependent on its degree of solubility in the formulation, particularly in the solvents used.
- the range of resin used in the present invention is from about 5% to about 70%, preferably from about 15% to about 45%, and even more preferably from about 20% to about 40%.
- compositions of the present invention may further comprise a fluid diorganopolysiloxane-based polymer to be combined with the organosiloxane resins.
- Said fluid diorganopolysiloxane-based polymers useful in the present invention span a large range of viscosities; from about 10 to about 10,000,000 centistokes (cSt) at 25°C.
- Some diorganopolysiloxane polymers useful in this invention exhibit viscosities greater than 10,000,000 centistokes (cSt) at 25 °C and therefore are characterized by manufacturer specific penetration testing.
- Examples of this characterization are GE silicone materials SE 30 and SE 63 with penetration specifications of 500-1500 and 250-600 (tenths of a millimeter) respectively.
- diorganopolysiloxane polymers comprising repeating units, where said units correspond to the formula (R2SiO) n , where R is a monovalent hydrocarbon radical containing from 1 to 6 carbon atoms, preferably selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t- butyl, amyl, hexyl, vinyl, allyl, cyclohexyl, amino alkyl, phenyl, fluoroalkyl and mixtures thereof.
- R is a monovalent hydrocarbon radical containing from 1 to 6 carbon atoms, preferably selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t- butyl, amyl, hexyl, vinyl, allyl, cyclohexyl, amino alkyl, phenyl, fluoroalkyl
- the fluid diorganopolysiloxane polymers employed in the present invention may contain one or more of these hydrocarbon radicals as substituents on the siloxane polymer backbone.
- the fluid diorganopolysiloxane polymers may be terminated by triorganosilyl groups of the formula (R ⁇ Si) where
- R 1 is a radical selected from the group consisting of monovalent hydrocarbons containing from 1-6 carbon atoms, hydroxyl groups, alkoxyl groups and mixtures thereof.
- the fluid diorganopolysiloxane polymer must be compatible in solution with the organosiloxane resin and the volatile carrier.
- compatible refers to the formation of a single phase solution when the fluid diorganopolysiloxane polymer, the organosiloxane resin and the volatile carrier are mixed together in ratios required for a specific formulation.
- the lower viscosity fluid diorganopolysiloxane polymers (viscosity of about 10 to 100cSt.) are particularly useful when using ethanol as the principal volatile carrier.
- Silicone gum corresponds to the formula:
- R is a methyl group
- Fluid diorganopolysiloxane polymers such as these are commercially available, for example, SE 30 silicone gum and SF96 silicone fluid available from the General Electric Company. Similar materials can also be obtained from Dow Corning and from Wacker Silicones.
- dimethicone copolyol to modify film forming characteristics as desired.
- the dimethicone copolyol can be further characterized as polyalkylene oxide modified polydimethysiloxanes, such as manufactured by the Witco Corporation under the trade name Silwet. Similar materials can be obtained from Dow Corning, Wacker Silicones and Goldschmidt Chemical Corporation as well as other silicone manufacturers.
- the ratio of organosiloxane resin to fluid diorganopolysiloxane-based polymer is preferably from about 15:1 to about 1 :15, more preferably from about 2:1 to about 8:1 , and still more preferably from about 4:1 to about 6:1.
- the organosiloxane resin and the fluid diorganosiloxane-based polymer above must be easily transferred to the oral cavity surfaces, such as to the tooth enamel.
- a carrier specifically a volatile carrier which must quickly volatilize from the oral cavity surfaces, leaving a film on the application surfaces.
- the volatile carrier must solubilize the organosiloxane resin and if present in the composition, the fluid diorganosiloxane-based polymer.
- the volatile carrier comprises from about 10% to about 90%, preferably from about 15% to about 80%, and more preferably from about 20% to about
- the volatile carrier of the present invention is selected from the group consisting of hydrocarbon oils, volatile silicones, non-hydrocarbon solvents, and mixtures thereof.
- Hydrocarbon oils useful in the present invention include those having boiling points in the range of 60-260°C, more preferably hydrocarbon oils having from about C ⁇ to about C20 chain lengths, most preferably Cs to C20 isoparaffins.
- isoparaffins most preferred are selected from the group consisting of isododecane, isohexadecane, isoeocosane, 2,2,4-trimethylpentane, 2,3-dimethylhexane and mixtures thereof.
- isododecane available as, for example, Permethyl 99A from Permethyl Corporation corresponding to the formula:
- Preferred volatile silicone fluids include cyclomethicones having 3, 4 and 5 membered ring structures corresponding to the formula:
- Such volatile silicones include 244 Fluid, 344 Fluid and 245 Fluid, and 345 Fluid all from Dow Corning Corporation.
- non-hydrocarbon solvents useful herein include esters, ketones, alcohols, fluorocarbons and fluorocarbon ethers having boiling points in the range of 60 to 200 °C.
- Non-hydrocarbon solvents or mixtures thereof particularly useful include those that are capable of solubilizing the resin and/or the diorganopolysiloxane-based polymer.
- solvents include but are not limited to ethanol, acetone, butanone, ethyl acetate, propyl acetate, amyl acetate, ethyl butyrate, methyl nonafluoroisobutyl ether, methyl nonafluorobutyl ether, and mixtures thereof.
- non-hydrocarbon solvents are readily available such as ethyl acetate and methyl ethyl ketone, both supplied by J. T. Baker of Phillispburg, N.J, and HFE (a mixture of methyl nonafluoroisobutyl ether and methyl nonafluorobutyl ether), supplied by the 3M Company.
- compositions further comprise a rheology modifier which inhibits settling and separation of components or controls settling in a manner which facilitates re-dispersion and may control rheological flow properties.
- Suitable rheology modifiers herein include organo modified clays, silicas, polyethylene, and mixtures thereof.
- the preferred organophilic clays comprise quaternium-18 hectorite or Stearalkonium hectorite, such as Bentone 27 and 38TM from Rheox, organoclay dispersion such as Bentone ISD gel TM; or bentonite organo modified clays such as Bentone 34TM from Rheox or the Claytone SeriesTM from Southern Clay Products; and mixtures thereof.
- the preferred silicas may be fumed silica such as the Aerosil TM series from Degussa or the Cab-o-sil TM series from Cabot Corporation, silica gels such as the Sylodent TM or Sylox TM series from W. R. Grace & Co. or precipitated silica such as Zeothix 265 from J. M. Huber Corporation.
- fumed silica such as the Aerosil TM series from Degussa or the Cab-o-sil TM series from Cabot Corporation
- silica gels such as the Sylodent TM or Sylox TM series from W. R. Grace & Co.
- precipitated silica such as Zeothix 265 from J. M. Huber Corporation.
- the rheology modifier is preferably present in the composition at a level of from about 0.1 % to about 30%, preferably from about 0.5% to about 10%, and even more preferably about 1 % to about 3% of the composition.
- the oral care substance preferably contains an active at a level where upon directed use, the benefit sought by the wearer is promoted without detriment to the oral surface to which it is applied.
- actives include, but, are not limited to, appearance and structural changes to teeth, whitening, stain bleaching, stain removal, plaque removal, tartar removal, cavity prevention and treatment, inflamed and/or bleeding gums, mucosal wounds, lesions, ulcers, aphthous ulcers, cold sores, tooth abscesses, and the elimination of mouth malodor resulting from the conditions above and other causes such as microbial proliferation.
- Suitable oral care substances include any material that is generally considered safe for use in the oral cavity and that provides changes to the overall appearance and/or health of the oral cavity.
- the level of oral care substance in the compositions of the present invention is generally, unless specifically noted, from about 0.01 % to about 50%, preferably from about 0.1% to about 20%, more preferably from about 0.5% to about 10%, and even more preferably from about 1 % to about 7%, by weight of the composition.
- Oral care compositions or substances of the present invention may include many of the actives previously disclosed in the art. The following is a non-limiting list of oral care actives that may be used in the present invention.
- Teeth whitening actives may be included in the oral care substance of the present invention.
- the actives suitable for whitening are selected from the group consisting of the peroxides, metal chlorites, perborates, percarbonates, peroxyacids, persulfates, and combinations thereof.
- Suitable peroxide compounds include hydrogen peroxide, urea peroxide, calcium peroxide, carbamide peroxide, and mixtures thereof. Most preferred is carbamide peroxide.
- Suitable metal chlorites include calcium chlorite, barium chlorite, magnesium chlorite, lithium chlorite, sodium chlorite, and potassium chlorite. Additional whitening actives may be hypochlorite and chlorine dioxide.
- the preferred chlorite is sodium chlorite.
- a preferred percarbonate is sodium percarbonate.
- Preferred persulfates are xones.
- Anti-tartar agents known for use in dental care products include phosphates.
- Phosphates include pyrophosphates, polyphosphates, polyphosphonates and mixtures thereof.
- Pyrophosphates are among the best known for use in dental care products. Pyrophosphate and polyphosphate ions are delivered to the teeth derive from pyrophosphate polyphosphate salts.
- the pyrophosphate salts useful in the present compositions include the dialkali metal pyrophosphate salts, tetra-alkali metal pyrophosphate salts, and mixtures thereof.
- Disodium dihydrogen pyrophosphate Na2H2P2 ⁇ 7 > tetrasodium pyrophosphate (Na4P2 ⁇ 7), and tetrapotassium pyrophosphate (K4P2O7) in their unhydrated as well as hydrated forms are the preferred species. While any of the above mentioned pyrophosphate salts may be used, tetrasodium pyrophosphate salt is preferred. Sodium polyphosphate and triethanolamine polyphosphates, for example, are preferred.
- pyrophosphate salts are described in more detail in Kirk & Othmer, Encyclopedia of Chemical Technology, Third Edition, Volume 17, Wiley- Interscience Publishers (1982). Additional anticalculus agents include pyrophosphates or polyphosphates disclosed in U.S. Patent No. 4,590,066 issued to Parran & Sakkab on May 20, 1986; polyacrylates and other polycarboxylates such as those disclosed in U.S. Patent No. 3,429,963 issued to Shedlovsky on February 25, 1969 and U.S. Patent No. 4,304,766 issued to Chang on December 8, 1981 ; and U.S. Patent No.
- Anticalculus phosphates include potassium and sodium pyrophosphates; sodium tripolyphosphate; diphosphonates, such as ethane-1-hydroxy-1 ,1-diphosphonate, 1- azacycloheptane-1 ,1-diphosphonate, and linear alkyl diphosphonates; linear carboxylic acids; and sodium zinc citrate.
- Agents that may be used in place of or in combination with the pyrophosphate salt include such known materials as synthetic anionic polymers including polyacrylates and copolymers of maleic anhydride or acid and methyl vinyl ether (e.g., Gantrez), as described, for example, in U.S. Patent 4,627,977, to Gaffar et al.; as well as, e.g., polyamino propoane sulfonic acid (AMPS), zinc citrate trihydrate, polyphosphates (e.g., tripolyphosphate; hexametaphosphate), diphosphonates (e.g., EHDP; AHP), polypeptides (such as polyaspartic and polyglutamic acids), and mixtures thereof. 3.
- synthetic anionic polymers including polyacrylates and copolymers of maleic anhydride or acid and methyl vinyl ether (e.g., Gantrez), as described, for example, in U.S. Patent 4,627,977, to Gaffar
- Fluoride ion sources are well known for use in oral care compositions as anticaries agents. Fluoride ions are contained in a number of oral care compositions for this purpose, particularly toothpastes. Patents disclosing such toothpastes include U.S. Pat. No. 3,538,230, Nov. 3, 1970 to Pader et al; U.S. Pat. No. 3,689,637, Sept. 5, 1972 to Pader; U.S. Pat. No. 3,711 ,604, Jan 16, 1973 to Colodney et al; U.S. Pat. No. 3,911 ,104, Oct. 7, 1975 to Harrison; U.S. Pat. No. 3,935,306, Jan. 27, 1976 to Roberts et al; and U.S. Pat. No. 4,040,858, Aug. 9, 1977 to Wason.
- fluoride ions to dental enamel serves to protect teeth against decay.
- fluoride ion-yielding materials can be employed as sources of soluble fluoride in the instant compositions. Examples of suitable fluoride ion-yielding materials are found in Briner et al; U.S. Pat. No. 3,535,421 ; issued Oct. 20, 1970 and Widder et al; U.S. Pat. No. 3,678,154; issued July 18, 1972.
- Preferred fluoride ion sources for use herein include sodium fluoride, potassium fluoride and ammonium fluoride. Sodium fluoride is particularly preferred.
- the instant compositions provide from about 50 ppm to 10,000 ppm, more preferably from about 100 to 3000 ppm, of fluoride ions in the compositions that contact dental surfaces when used with the delivery system of the present invention.
- Anti-microbial agents can also be present in the oral care compositions or substances of the present invention. Such agents may include, but are not limited to, 5-chloro-2-(2,4-dichlorophenoxy)-phenol, commonly referred to as triclosan, and described in The Merck Index. 11th ed. (1989), pp. 1529 (entry no. 9573) in U.S. Patent No. 3,506,720, and in European Patent Application No. 0,251 ,591 of Beecham Group, PLC, published January 7, 1988; phthalic acid and its salts including, but not limited to those disclosed in U.S. Pat. 4,994,262, Feb.
- magnesium monopotassium phthalate chlorhexidine (Merck Index, no. 2090), alexidine (Merck Index, no. 222; hexetidine (Merck Index, no. 4624); sanguinarine (Merck Index, no. 8320); benzalkonium chloride (Merck Index, no. 1066); salicylanilide (Merck Index, no. 8299); domiphen bromide (Merck Index, no. 3411); cetylpyridinium chloride (CPC) (Merck Index, no.
- TPC tetradecylpyridinium chloride
- TDEPC N-tetradecyl-4-ethylpyridinium chloride
- octenidine delmopinol, octapinol, and other piperidino derivatives
- octenidine delmopinol, octapinol, and other piperidino derivatives
- octapinol and other piperidino derivatives
- octenidine delmopinol, octapinol, and other piperidino derivatives
- iron preparations zinc/stannous ion agents
- antibiotics such as augmentin, amoxicillin, tetracycline, doxycycline, minocycline, and metronidazole
- analogs and salts of the above essential oils including thymol, geraniol, carvacrol, citral, hinokitiol, eucalyptol, catechol (particularly 4- ally
- Anti-inflammatory agents can also be present in the oral care compositions or substances of the present invention.
- Such agents may include, but are not limited to, non-steroidal anti-inflammatory agents or NSAIDs such as ketorolac, flurbiprofen, ibuprofen, naproxen, indomethacin, aspirin, ketoprofen, piroxicam and meclofenamic acid.
- NSAIDs such as Ketorolac are claimed in U.S. Patent 5,626,838, issued May 6, 1997.
- Disclosed therein are methods of preventing and, or treating primary and reoccurring squamous cell carcinoma of the oral cavity or oropharynx by topical administration to the oral cavity or oropharynx an effective amount of an NSAID.
- Nutrients may improve the condition of the oral cavity and can be included in the oral care compositions or substances of the present invention. Nutrients include minerals, vitamins, oral nutritional supplements, enteral nutritional supplements, and mixtures thereof.
- Minerals that can be included with the compositions of the present invention include calcium, phosphorus, fluoride, zinc, manganese, potassium and mixtures thereof. These minerals are disclosed in Drug Facts and Comparisons (loose leaf drug information service), Wolters Kluer Company, St. Louis, Mo., ⁇ 1997, pp10-17.
- Vitamins can be included with minerals or used separately. Vitamins include Vitamins C and D, thiamine, riboflavin, calcium pantothenate, niacin, folic acid, nicotinamide, pyridoxine, cyanocobalamin, para-aminobenzoic acid, bioflavonoids, and mixtures thereof. Such vitamins are disclosed in Drug Facts and Comparisons (loose leaf drug information service), Wolters Kluer Company, St. Louis, Mo., ⁇ 1997, pp. 3-10. Oral nutritional supplements include amino acids, lipotropics, fish oil, and mixtures thereof, as disclosed in Drug Facts and Comparisons (loose leaf drug information service), Wolters Kluer Company, St.
- Amino acids include, but, are not limited to L-Tryptophan, L-Lysine, Methionine, Threonine, Levocamitine or L- camitine and mixtures thereof.
- Lipotropics include, but, are not limited to choline, inositol, betaine, linoleic acid, linolenic acid, and mixtures thereof.
- Fish oil contains large amounts of Omega-3 (N-3) Polyunsatu rated fatty acids, eicosapentaenoic acid and docosahexaenoic acid.
- Entenal nutritional supplements include, but, are not limited to protein products, glucose polymers, corn oil, safflower oil, medium chain triglycerides as disclosed in Drug Facts and Comparisons (loose leaf drug information service), Wolters Kluer Company, St. Louis, Mo., ⁇ 1997, pp. 55-57.
- Other materials that can be used with the present invention include commonly known mouth and throat products. Such products are disclosed in Drug Facts and Comparisons (loose leaf drug information service), Wolters Kluer Company, St. Louis, Mo., ⁇ 1997, pp. 520b-527. These products include, but, are not limited to anti-fungal, antibiotic and analgesic agents.
- Antioxidants are generally recognized as useful in compositions such as those of the present invention. Antioxidants are disclosed in texts such as Cadenas and Packer, The Handbook of Antioxidants. ⁇ 1996 bv Marcel Dekker. Inc. Antioxidants that may be included in the oral care composition or substance of the present invention include, but are not limited to Vitamin E, ascorbic acid, Uric acid, carotenoids, Vitamin A, flavonoids and polyphenols, herbal antioxidants, melatonin, aminoindoles, lipoic acids and mixtures thereof.
- Histamine-2 (H-2 or H2) receptor antagonist compounds may be used in the oral care composition of the present invention.
- selective H-2 antagonists are compounds that block H-2 receptors, but do not have meaningful activity in blocking histamine- 1 (H-1 or H1 ) receptors.
- Selective H-2 antagonists stimulates the contraction of smooth muscle from various organs, such as the gut and bronchi; this effect can be suppressed by low concentrations of mepyramine - a typical antihistaminic drug.
- the pharmacological receptors involved in these mepyramine-sensitive histamine responses have been defined as H-1 receptors (Ash, A.S.F. & H.O. Schild, Brit. J. Pharmacol Chemother., Vol.
- Histamine also stimulates the secretion of acid by the stomach (Loew, E.R. & O. Chickering, Proc. Soc. Exp. Biol. Med., Vol. 48 (1941), p. 65), increases the heart rate (Trendelenburg, U., J. Pharmacol., Vol. 130 (1960), p. 450), and inhibits contractions in the rat uterus (Dews, P.B. & J.D.P. Graham, Brit. J. Pharmacol. Chemother., Vol. 1 (1946), p. 278); these actions cannot be antagonized by mepyramine and related drugs.
- the H-2 antagonists useful in the oral care compositions or substances are those that blockade the receptors involved in mepyramine-insensitive, non-H-1 (H-2), histamine responses, and do not blockade the receptors involved in mepyramine-sensitive histamine responses.
- Selective H-2 antagonists are those compounds found to be H-2 antagonists through their performance in classical preclinical screening tests for H-2 antagonist function.
- Selective H-2 antagonists are identified as compounds which can be demonstrated to function as competitive or non-competitive inhibitors of histamine-mediated effects in those screening models specifically dependent upon H-2 receptor function, but to lack significant histamine antagonist activity in those screening models dependent upon H-1 receptor function. Specifically, this includes compounds that would be classified as described by Black, J.W., W.A.M. Duncan, C.J. Durant, C.R. Ganellin & E.M. Parsons, "Definition and Antagonism of Histamine H2-Receptors", Nature, Vol. 236 (April 21 , 1972), pp.
- H-2 antagonists if assessed as described by Black through testing with the guinea pig spontaneously beating right atria in vitro assay and the rat gastric acid secretion in vivo assay, but shown to lack in significant H-1 antagonist activity relative to H-2 antagonist activity, if assessed as described by Black with either the guinea pig ileum contraction in vitro assay or the rat stomach muscle contraction in vivo assay.
- selective H-2 antagonists demonstrate no significant H-1 activity at reasonable dosage levels in the above H-1 assays. Typical reasonable dosage level is the lowest dosage level at which 90% inhibition of histamine, preferably 99% inhibition of histamine, is achieved in the above H-2 assays.
- Selective H-2 antagonists include compounds meeting the above criteria which are disclosed in U.S. Patents 5,294,433 and 5,364,616 Singer et al., issued 3/15/94 and 11/15/94 respectively and assigned to Procter & Gamble, wherein the selective H-2 antagonist is selected from the group consisting of cimetidine, etintidine, ranitidine, ICIA-5165, tiotidine, ORF-17578, lupitidine, donetidine, famotidine, roxatidine, pifatidine, lamtidine, BL-6548, BMY-25271 , zaltidine, nizatidine, mifentidine, BMY-52368 (SKF-94482), BL-6341A, ICI- 162846, ramixotidine, Wy-45727, SR-58042, BMY-25405, loxtidine, DA-4634, bisfentidine, sufotidine, ebrotidine, HE-30-
- cimetidine (SKF- 92334), N-cyano-N'-methyl-N"-(2-(((5-methyl-1 H-imidazol-4- yl)methyl)thio)ethyl)guanidine:
- Cimetidine is also disclosed in the Merck Index. 11th edition (1989), p. 354 (entry no. 2279), and Physicians' Desk Reference. 46th edition (1992), p. 2228.
- Related preferred H-2 antagonists include burimamide and metiamide.
- Analgesic Actives Anti-pain or desensitizing agents can also be present in the oral care compositions or substances of the present invention. Such agents may include, but are not limited to, strontium chloride, potassium nitrate, natural herbs such as gall nut, Asarum, Cubebin, Galanga, scutellaria, Liangmianzhen, Baizhi, etc. 11.
- Antiviral actives useful in the present composition include any know actives that are routinely use to treat viral infections. Such anti-viral actives are disclosed in Drug Facts and Comparisons (loose leaf drug information service), Wolters Kluer Company, St. Louis, Mo., ⁇ 1997, pp. 402(a)-407(z), incorporated herein by reference in its entirety. Specific examples include anti-viral actives disclosed in U.S. Patent 5,747,070, issued May 5, 1998 to Satyanarayana Majeti, incorporated herein by reference in its entirety. Said Patent discloses the use of stannous salts to control viruses.
- stannous salts and other anti-viral actives are described in detail in Kirk & Othmer, Encyclopedia of Chemical Technology, Third Edition, Volume 23, Wiley-lnterscience Publishers (1982), pp. 42-71 , incorporated herein by reference in its entirety.
- the stannous salts that may be used in the present invention would include organic stannous carboxylates and inorganic stannous halides. While stannous fluoride may be used, it is typically used only in combination with another stannous halide or one or more stannous carboxylates or another therapeutic agent. 12.
- Other Ingredients include organic stannous carboxylates and inorganic stannous halides. While stannous fluoride may be used, it is typically used only in combination with another stannous halide or one or more stannous carboxylates or another therapeutic agent. 12.
- Additional components include, but are not limited to, flavoring agents, sweetening agents, xylitol, opacifiers, coloring agents, surfactants, and chelants such as ethylenediaminetetraacetic acid.
- Suitable flavoring agents include, but are not limited to, oil of peppermint, oil of sassafras, clove bud oil, peppermint, menthol, anethole, thymol, methyl salicylate, eucalyptol, cassia, 1- menthyl acetate, sage, eugenol, parsley oil, oxanone, oil of wintergreen, alpha- irisone, oil of spearmint, marjoram, lemon, orange, propenyl guaethol, cinnamon, and mixtures thereof.
- Pigments may also added to the compositions herein to more precisely indicate the locations at which the composition has actually been applied, allowing the user to apply the composition more thoroughly or evenly. However, such pigments are not intended to mask stains that may exist on the tooth surfaces. These additional ingredients can also be used in place of the compounds disclosed above.
- MQ resin available as 1170-002 from General Electric.
- Dimethicone gum available as SE 30 or SE 63 from General Electric available as SE 30 or SE 63 from General Electric.
- the percentage of each individual solvent component in the mixed solvent systems can vary from 0 to 100%, respectively.
- MQ resin available as 1170-002 from General Electric.
- Dimethicone gum available as SE 30 from General Electric is available as SE 30 from General Electric.
- DC-200/350 is: dimethylpolysiloxane, CAS# 9016-00-6, from Dow Corning.
- HFE-7100 is a mixture of Methyl Nonafluoroisobutyl Ether, CAS# 163702-08- 7 and Methyl Nonafluorobutyl Ether, CAS# 163702-07-6, manufactured by 3M Co.
- Aerosil 200 is silicon dioxide (chemically prepared), CAS# 112945-52-5, from Degussa AG.
- the delivery compositions of Tables 1 and 2 are non-aqueous.
- the oral care substances are dispersed or dissolved in a solution comprising the organosiloxane resin, the fluid diorganopolysiloxane-based polymer, the volatile carrier, and the rheology modifier.
- compositions of Tables 1 and 2 are suitably prepared as follows.
- organosiloxane resin solution for example, 43.7%
- MQ resin solution in isododecane or in a 50/50 mixture of ethyl acetate and butanone (or in a mixture of ethyl acetate, propyl acetate and HFE) are mixed with 147.30 grams of fluid diorganopolysiloxane polymer solution (for example,
- the oral care substances are then dispersed in the resin/gum mixture. This method may be carried out without the presence of the silicone gum.
- the delivery compositions of Tables 3-6 are suitably prepared as follows. Add the solvents into a container suitable to minimize solvent loss. Add the rheology modifiers and mix until well dispersed. Add the silicone resin and mix until completely dissolved. Add the silicone gum and/or silicone fluids and mix until completely dissolved. At this time add any salts such as sodium percarbonate and/or other oral care actives, aesthetic ingredients such as opacifiers, sweeteners, dyes, and flavors. Continue mixing until homogeneous. Additional high shear mixing may be used to promote the mixing. Pack into airtight containers.
- premixes of the silicone resin and/or the silicone gum may be prepared prior to incorporation into the final blending step to facilitate silicone dissolution and ease of manufacturing.
- the order of ingredient addition may also vary such as the addition of the rheology modifier(s) may be moved to a later step allowing lower viscosity to be maintained until the later stages of the blending step.
- MQ resin available as 1170-002 from General Electric.
- the percentage of ethyl acetate and butanone in the mixed system can vary from 0 to 100%, respectively; or a mixture of HFE, propyl acetate, and ethyl acetate.
- Bentone 27 available from Rheox.
- the user need only apply a delivery composition that contains the oral care substance or substances necessary in order to obtain a desired effect, e.g., whitening, breath freshening, caries prevention, pain relief, gum health, tartar control, etc., followed by a protective composition to the tooth surfaces in the areas desired.
- a desired effect e.g., whitening, breath freshening, caries prevention, pain relief, gum health, tartar control, etc.
- the compositions herein may also be applied to other surfaces of the oral cavity, such as the gingival or mucosal tissues, or to any other oral cavity surface.
- the compositions herein can be applied with a brush, a pen applicator, a doe's foot applicator, or the like, or even with the fingers.
- a film containing the oral care substance quickly forms on the surface to which the delivery composition has been applied. Then, the user applies the protective composition to the same surfaces, on top of the delivery composition. Similarly, the protective composition quickly forms a film.
- Prolonged delivery of the oral care substance is made possible as the oral care substance is released from the film formed by the delivery composition over time.
- the protective composition protects the delivery composition from wearing off to prolong the wear of the delivery compositions and therefore to prolong the presence of the oral care substance in the oral cavity.
- the protective compositions force the oral care substance being released to act on the applied area, and inhibit it from being released elsewhere in the oral cavity or from being worn away by saliva, eating, etc.
- the protection efficacy provided by the protective composition depends on the amount of resin present, as well as the resin to polymer ratio and the polymer concentration in those compositions further comprising a fluid diorganopolysiloxane-based polymer. It is further believed that the protection efficacy is influenced by the specific oral care substance that is present in the delivery composition.
- any residual oral care substance or film may be easily removed by wiping, brushing or rinsing the oral surface after a desired period of time has elapsed, or in the normal course of tooth brushing or other oral care activities.
- the wear time of the systems herein is from about 2 hours to 10 hours, regardless of the reactivity of the oral care substance.
- the systems are almost unnoticeable when applied to the oral cavity.
- the user may or may not choose to brush the teeth or rinse the mouth before applying the compositions.
- the surfaces of the oral cavity are neither required to be dried nor to be excessively wet with saliva or water before the compositions are applied.
- adhesion to the tooth enamel surfaces will be improved if the teeth are dry when the compositions are applied.
- the present invention relates not only to methods for delivering an oral care substance to the oral cavity of a human, but also to methods of delivering an oral care substance to the oral cavity of an animal, e.g., household pets or other domestic animals, or animals kept in captivity.
Abstract
Description
Claims
Applications Claiming Priority (9)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
WOPCT/US99/15131 | 1999-07-02 | ||
WOPCT/US99/15130 | 1999-07-02 | ||
US9915131 | 1999-07-02 | ||
US9915130 | 1999-07-02 | ||
WOPCT/US00/15891 | 2000-06-09 | ||
PCT/US2000/015891 WO2001001940A1 (en) | 1999-07-02 | 2000-06-09 | Compositions comprising organosiloxane resins for delivering oral care substances |
PCT/US2000/015890 WO2001001939A1 (en) | 1999-07-02 | 2000-06-09 | Compositions comprising organosiloxane resins for delivering oral care substances |
WOPCT/US00/15890 | 2000-06-09 | ||
PCT/US2000/018189 WO2001001942A1 (en) | 1999-07-02 | 2000-06-30 | Systems comprising organosiloxane resins for delivering oral care substances and for prolonging such delivery |
Publications (2)
Publication Number | Publication Date |
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EP1196137A1 true EP1196137A1 (en) | 2002-04-17 |
EP1196137B1 EP1196137B1 (en) | 2004-12-22 |
Family
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Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
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EP00945085A Expired - Lifetime EP1196137B1 (en) | 1999-07-02 | 2000-06-30 | Systems comprising organosiloxane resins for delivering oral care substances and for prolonging such delivery |
EP00945084A Expired - Lifetime EP1200064B1 (en) | 1999-07-02 | 2000-06-30 | Delivery system for oral care compositions comprising organosiloxane reins using a removable backing strip |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP00945084A Expired - Lifetime EP1200064B1 (en) | 1999-07-02 | 2000-06-30 | Delivery system for oral care compositions comprising organosiloxane reins using a removable backing strip |
Country Status (22)
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US (1) | USRE42126E1 (en) |
EP (2) | EP1196137B1 (en) |
JP (1) | JP3927030B2 (en) |
KR (1) | KR20020032521A (en) |
CN (1) | CN1204875C (en) |
AT (2) | ATE238766T1 (en) |
AU (3) | AU5907500A (en) |
BR (1) | BR0012145A (en) |
CA (2) | CA2373983C (en) |
CZ (1) | CZ20014709A3 (en) |
DE (2) | DE60002471T2 (en) |
ES (1) | ES2199168T3 (en) |
HK (1) | HK1047035B (en) |
HU (1) | HUP0201620A3 (en) |
IL (1) | IL147265A (en) |
MA (1) | MA25681A1 (en) |
MX (1) | MXPA02000262A (en) |
NO (1) | NO20020004L (en) |
PL (1) | PL200936B1 (en) |
RU (1) | RU2223746C2 (en) |
SK (1) | SK19412001A3 (en) |
WO (3) | WO2001001942A1 (en) |
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- 2000-06-30 CA CA002373983A patent/CA2373983C/en not_active Expired - Fee Related
- 2000-06-30 CN CNB008099847A patent/CN1204875C/en not_active Expired - Fee Related
- 2000-06-30 AU AU59075/00A patent/AU5907500A/en not_active Abandoned
- 2000-06-30 CZ CZ20014709A patent/CZ20014709A3/en unknown
- 2000-06-30 US US10/927,655 patent/USRE42126E1/en not_active Expired - Fee Related
- 2000-06-30 RU RU2002102710/15A patent/RU2223746C2/en not_active IP Right Cessation
- 2000-06-30 AU AU59073/00A patent/AU5907300A/en not_active Abandoned
- 2000-06-30 MX MXPA02000262A patent/MXPA02000262A/en active IP Right Grant
- 2000-06-30 PL PL357159A patent/PL200936B1/en not_active IP Right Cessation
- 2000-06-30 DE DE60002471T patent/DE60002471T2/en not_active Expired - Lifetime
- 2000-06-30 ES ES00945084T patent/ES2199168T3/en not_active Expired - Lifetime
- 2000-06-30 EP EP00945085A patent/EP1196137B1/en not_active Expired - Lifetime
- 2000-06-30 EP EP00945084A patent/EP1200064B1/en not_active Expired - Lifetime
- 2000-06-30 KR KR1020027000033A patent/KR20020032521A/en not_active Application Discontinuation
- 2000-06-30 AT AT00945084T patent/ATE238766T1/en not_active IP Right Cessation
- 2000-06-30 CA CA002375093A patent/CA2375093C/en not_active Expired - Fee Related
- 2000-06-30 WO PCT/US2000/018189 patent/WO2001001942A1/en active IP Right Grant
- 2000-06-30 AU AU59074/00A patent/AU768471B2/en not_active Ceased
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- 2000-06-30 JP JP2001507453A patent/JP3927030B2/en not_active Expired - Lifetime
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2002
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